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. 1980 May 16;289(1036):191-5.
doi: 10.1098/rstb.1980.0037.

A stereocontrolled, enantiomerically specific total synthesis of thienamycin

T N Salzmann, R W Ratcliffe, F A Bouffard, B G Christensen

A stereocontrolled, enantiomerically specific total synthesis of thienamycin

T N Salzmann et al. Philos Trans R Soc Lond B Biol Sci. .

Abstract

A versatile stereocontrolled total synthesis of thienamycin starting from L-aspartic acid is reported. Stereocontrol is achieved by potassium tri-sec-butylborohydride reduction of a thermodynamically formed 3 alpha-acetylazetidinone intermediate. The key [3.2.0] bicyclic ring system is prepared by a metal catalyzed carbene insertion reaction.

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